46277-27-4Relevant academic research and scientific papers
Benzimidazole-derived ATP analogues as potential glutamine synthetase inhibitors
Gxoyiya, Babalwa S. B.,Kaye, Perry T.,Kenyon, Colin
experimental part, p. 2578 - 2587 (2010/10/03)
A series of mono-and dihydroxyalkyl-and-alkyloxybenzimidazoles and their phosphorylated derivatives have been prepared as adenosine triphoshate analogues for investigation as potential M. Tb. glutamine synthetase inhibitors. Taylor & Francis Group, LLC.
Synthesis of analogs of L-valacyclovir and determination of their substrate activity for the oligopeptide transporter in Caco-2 cells
Friedrichsen, Gerda Marie,Chen, Weiqing,Begtrup, Mikael,Lee, Chao-Pin,Smith, Philip L.,Borchardt, Ronald T.
, p. 1 - 13 (2007/10/03)
L-Valacyclovir, a prodrug of acyclovir, is a substrate for the peptide transporter (PepT1) in the intestinal mucosa, which accounts for its higher than expected oral bioavailability. The substrate activity of L-valacyclovir for PepT1 is surprising, particularly when one considers that the molecule has the structural features of a nucleoside rather than a peptide. In an attempt to better understand the structure-transport relationships (STR) for the interactions of L-valacyclovir with PepT1, analogs of this molecule with structural changes in the guanine moiety were synthesized and their substrate activity for PepT1 in Caco-2 cell monolayers was determined. The analogs synthesized include those that had the guanine moiety of L-valacyclovir substituted with purine, benzimidazole, and 7-azaindole. All three analogs (purine, benzimidazole, and 7-azaindole) exhibited affinity for PepT1 in binding studies, but only the purine analog (as the L-valine ester) showed PepT1-associated transcellular transport across Caco-2 cell monolayers. The benzimidazole and 7-azaindole analogs (as their L-valine esters) were rapidly metabolized by esterase when applied to the apical surface of Caco-2 cells, which probably explains their low penetration as the intact prodrugs via PepT1.
Acyclic Analogs of Nucleosides. Synthesis of Hydroxyalkylbenzimidazoles and -Benzotriazoles
Yavorskii, A. E.,Stetsenko, A. V.,Zavgorodnii, S. G.,Florent'ev, V. L.
, p. 163 - 167 (2007/10/02)
Condensation of trimethylsilyl derivatives of benzimidazole and benzotriazole with alkylating agents in the presence of trimethylsilyl trifluoromethanesulfonate or SnCl4, or direct alkylation of the sodium salts of benzimidazole and benzotriazole, gives 1-(2,3-dihydroxypropyl)-, 1-(3-hydroxy-2-oxabutyl)-, 1-(3-hydroxymethyl-4-hydroxy-2-oxabutyl)-, and 1-(1,5-dihydroxy-3-oxapent-2-yl)benzimidazole and -benzotriazole.
